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Undiscovered Umbria to Cortona, Land of the Tuscan Sun

No doubt you'll arrive with certain expectations. After all, artists and writers have sung the praises of Tuscany and Umbria for centuries. But somehow it's still a surprise, the sensory feast that surrounds you. You're still floored by the beauty of silvery olive groves and endless acres of vineyards. By the slow pace of life. By the symphony of flavors in traditional dishes passed down through generations. By the chefs and vintners who are proud to share their talents. And the sheer passione of the locals. Expectations exceeded? Just another day in the heart of Italy.

Itinerary

Days
1-2Medieval flavor and ancient traditions await in charming hilltop towns The only hill town on the valley floor, Montefalco is a great spot for soaking up views of Assisi to the north and Spoleto in the south Coast downhill to a bountiful picnic lunch in the heart of the Sagrantino wine (Umbria's "big red") production zone Dine and wander in timeless Spello, perhaps pausing to browse for ceramics, linens and olive wood pieces Beauty abounds in Assisi, from the stunning Basilica of Saint Francis to the verdant valley below.

Day
3Imagine you're in a postcard as you pedal along a winding road flanked by bright red poppies, cypress trees and undulating hills Spin through the Umbrian countryside, where fortified towns and distant Mount Subasio provide a dramatic backdrop We're treated like royalty at the luxurious Borgo dei Conti Resort, a Relais & Châteaux fortress-turned-castle dating back to the 13th century.

Days
4-6Welcome to Tuscany! Cruise past olive groves and sunflower fields to La Braccesca wine estate for an exclusive cooking demo and lunch Pedal through the Chiana Valley, where white Chianina cows graze Bike to historic hilltop Cortona, surrounded by 3,000-year-old Etruscan walls, and the setting for Under the Tuscan Sun Taste splendid wines, like Sagrantino, Montefalco Rosso and Vino Nobile di Montepulciano Giovanni, our longtime local guide, leads us through this celebrated town Savor a classic Tuscan landscape during an easy ride past ancient farmhouses, vast wheat fields and cypress-lined roads.

La Corte dei Papi

Guest Reviews About This Trip

For us it was a truly amazing and educational experience. Loved the physical challenge, loved the cultural interactions and loved the way that the Backroads team made it appear effortless and that we were the only riders on the road, the only customers at the hotels and restaurants. A joy, every minute of it.

Robert Allison

This trip was wonderful! Our leaders were fabulous, the cycling was just challenging enough. The hotels were very comfortable, and the service was excellent. And the countryside was so incredibly beautiful - the food, the people - something I will remember for a very long time.

Barbara Page- San Marcos, CA

This truly was a remarkable, memorable trip. I feel that biking allowed us to truly experience Italy in an intimate way. We met people on the roadside picking mushrooms...we could see Tuscany, feel Tuscany, and smell Tuscany!

This Trip Is Rated Level 1-4

Routes For All Abilities
Every Backroads trip is designed to appeal to a wide variety of
interests and fitness levels. We know your pace may vary from one
day to the next-and your traveling companion's may differ somewhat
from yours. So we present a range of mileage options, and each
day you decide exactly what and how much you want to do.

Daily Route Options

Day

EASYGOING

ACTIVE

AVID

Level 1

Level 2

Level 3

Level 4

Level 5

miles

feet gain

miles

feet gain

miles

feet gain

miles

feet gain

miles

feet gain

1

19

200

26

900

2

26*

600

41*

700

50

800

3

29*

2800

44

4400

57

5300

4

26*

1500

35

1800

42

1900

5

20*

1000

35*

1300

43

2300

Cortona Guided Walking Tour (1.5 Hours)

6

9*

300

16

400

note:

* Includes a shuttle

Private Trips Options & Pricing

Gather your favorite people to share a Backroads adventure on a ready-to-book Private Trip - featuring all the legendary Backroads hallmarks from expert leaders to unforgettable activities.

You can pick from a large selection of dates for your group of 8 or more. Call us for date availability.

If your party has fewer than 8 guests, or if your preferred date is not available, we'll create a departure just for you.